My first “happy ending”

This post continues a series of posts I’ve been writing about my descent into depravity, my loss of control over my sexuality. It begins with my origin myth, told here and here (and here), and continues with my first lap dances. In this post, I write about my first “sensual massage.” I’ve written a bit about the world of sensual massage before, but this post takes it from a very different, much more personal, angle.

It was a Saturday afternoon. The sun was shining, it was a beautiful Fall day. I was a little hung over from the night before. I’d been to a party, and hadn’t gotten laid. I was 27 or so – by this point in my life, most of the sex I had happened in the context of serial monogamy. I had broken up with a girlfriend a few weeks earlier, and hadn’t yet hooked up with the next. I always hoped I’d get laid at parties (doesn’t everyone?), but the truth is, the only way it ever happened for me was either with a friend, or as a “first date” with a friend of a friend, or a friend, who became a girlfriend. On this particular night, sex with a friend wasn’t happening, and neither was the start of a new relationship.

So it’s Saturday afternoon – I’m awake, a bit hung over, and horny. In a way that’s starting to feel desperate. By this time, I knew some things about myself, about my relationship to my desire: the way my horniness manifested, what I craved more than anything was the sensation of my hard cock’s being rubbed by an attractive woman. I didn’t want to fuck. I didn’t even (necessarily) want a blowjob. What I craved was touch. By this point, what I would usually do in such a circumstance was to go to the Harmony Theater for a lap dance or seven.

I leafed through the Village Voice (this was before the interwebs), the back pages of which, then and now, feature ads for a variety of erotic services. I’d never before paid for sex (other than for lap dances), and wasn’t sure about the mechanics of all this. I picked out an ad – it was an inobtrusive one, a little, two-line, thing – “sensual massage by college student” or some such. I dialed the number, and a woman picked up on the second ring.

“Hello?”

“Um. Hello. Um. Um. Do you have any, um, appointments, um, today?”

“Sure! What time would you like to come in?”

“Um. Now?”

“How about in 20 minutes, sweetie?”

“Um. Sure.”

She told me to call from a pay phone on a corner not far from my apartment when I arrived (yes, this was before cell phones, too).

I did.

She gave me an address, told me which buzzer to ring. The building was a regular apartment building, about twenty units, on a busy street of mixed commercial and residential uses (Lexington Avenue, in the 20s, for those of you who know New York). I rang the buzzer, the door opened, and in I went.

As I approached the door of the apartment, even before I could knock or ring the doorbell, it opened from the inside, revealing a darkly lit, but perfectly nice, apartment. The person opening the door stood behind it, beyond my view. I walked in, scared shitless.

Once I was far enough in for the door to close, she closed the door: before me stood Phoebe, a 5’6″ pale Asian-American woman, cute, maybe 25, in jeans and a t-shirt, with super-long jet-black hair. “Hi!” she said, bubbly. “I’m Phoebe!”

“N,” I mumbled, shaking her hand, awkward. There was a little fireplace with a fake fire burning in it – one of those light/fan/paper fake fires.

“Make yourself comfortable!” she said. Everything she said was followed by an exclamation point. She seemed genuinely happy – happy to see me, happy to be doing what(ever it was) she was about to do. I was perplexed. “You can just put your money in that envelope over there….” she said.

This was shameful, awful, embarrassing, humiliating, what we were about to do. Her nonchalance, her cheeriness, were in direct contrast to my nearly infinite mortification.

I inferred that “make yourself comfortable” meant, “Take off all your clothes and lie on your stomach on the massage table,” but I hesitated a bit when I got to my boxers. Suddenly I found myself wondering: was this really an erotic massage? Did she really expect me to get naked? Was she going to be offended? Was I going to be arrested?

I swallowed hard. In for a penny, in for a pound.

Off came my boxers, as I faced away from her. I climbed up on the table and lay down.

Once my boxers were off, she undressed – she swept her t-shirt off effortlessly in a gesture, revealing gorgeous A-cup breasts in an entirely unnecessary cotton bra. Her jeans came off, revealing a black thong. The first thong I’d ever seen in person, I’d guess, outside of a strip club. That was as far as she went, disrobing-wise. She trailed her fingers lightly on my back, and turned to grab something. “You’re cute,” she said. “Oil, lotion, or powder?”

“Excuse me?”

“Oil, lotion, or powder? Which would you like me to use?”

“Um. Lotion?”

“Ok, honey. Relax.”

A ridiculous request, but, in lieu of relaxing, I lay still.

She began to massage me. An utterly conventional massage in every way. Well, except that, to begin with, she was in her underwear and I was nude, and that, as the massage progressed, she would, occasionally, tickle my thighs, stray up to my balls, and just give them a gentle touch, tap, flick, stroke.

I don’t know if I was hard when, 45 minutes in, she said, “Would you like to turn over?”

I think the honest answer would have been, “NO! Are you out of your mind?”

But that’s not what I said, not what I did.

I rolled over, and as I did so, she took off her bra. Her breasts were gorgeous – perfect, round, with a mole on her right one toward the side. Yes, I still remember it like it was yesterday. (Remarkable, given the number of such “massages” I had over the intervening years. But I do.)

She reached over to the mantle above the fireplace, and grabbed a bottle of oil. She drizzled it onto my cock, which was definitely growing harder now. The oil was cold. But then she grabbed me. Her right hand started up and down my cock, her left hand cupped my balls, gently, gently.

The sensation she was giving me was unlike any I’d had previously. While I was fairly sexually adventurous, and experienced (I thought), in fact, shame had so deeply penetrated my every sexual encounter to date that I’d never imagined sexual pleasure could be something engaged in with a smile, joyfully, playfully.

“Is this good?” she asked.

I had no idea how to reply. It wasn’t that I was in ecstasy – I mean, it felt good, sure, but not earth-shattering good – just good. But the idea that if it weren’t good, I could tell her, that she wouldn’t react defensively, as if I’d criticized her – that wasn’t a reality I was ready to learn yet.

And I didn’t – it took years. And a whole lot of massages.

She stroked, and squeezed, and rubbed, and twisted. She placed my hand on her ass, told me to squeeze it. She moved toward me as I did so, moving her pussy (something I had never referred to as anything other than a “vagina” up til that point) toward my fingers, which instinctively recoiled.

She stroked harder, faster. I sensed that I was supposed to cum, and so I did, shooting cum all over the hand she placed expertly just in front of my cock moments earlier.

She rubbed it into my stomach, growling with satisfaction, as she continued tugging my cock gently for a few more moments.

She let go.

“May I get you a warm towel?”

“Sure.”

She came back with a warm washcloth, which she used to clean me up. I said nothing. She chattered – about Southern California, where she’s from, about college, about grad school, about her boyfriend (who didn’t know what she did for work).

I was in something of a trance. I had just paid for sex. I knew that. I was a pathetic loser who could only cum with a woman by paying her. I was ashamed, miserable.

This is brilliantly told, and I am also so impressed by your recollection of detail. Something I absolutely love about your blog is how well you delve into and retell these experiences. It’s not just the voyeur in me who is incredibly interested. And yet, what I really want to know is why, how, this came to be: “While I was fairly sexually adventurous, and experienced (I thought), in fact, shame had so deeply penetrated my every sexual encounter to date that I’d never imagined sexual pleasure could be something engaged in with a smile, joyfully, playfully.”

How can that be so? Perhaps that’s a topic for another post (in fact, I’m sure it is). But here’s the shortest of answers:

I was raised in a politically progressive environment, but I learned a couple of contradictory lessons from my parents:

1) All sexualities are natural, good and fine.
2) Except ours. Which are deeply shameful.
3) Sex is beautiful, and fun, and natural.
4) You should ONLY want to fuck a woman for her mind. Anything else? Misogynistic.

SO: I didn’t believe that my depravities – fooling around with guys, threesomes, foursomes, moresomes, were “wrong,” per se. I didn’t believe that anything I could do was wrong per se. But if I _wanted_ something? That was shameful….